NPASS Compound

Structure

CID43345 OpenBabel06191715372D 43 46 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 43 1 0 0 0 0 2 11 2 0 0 0 0 2 22 1 0 0 0 0 3 12 1 0 0 0 0 3 22 2 0 0 0 0 4 13 2 0 0 0 0 4 22 1 0 0 0 0 5 14 1 0 0 0 0 5 23 2 0 0 0 0 6 15 2 0 0 0 0 6 23 1 0 0 0 0 7 16 1 0 0 0 0 7 24 2 0 0 0 0 8 17 2 0 0 0 0 8 24 1 0 0 0 0 9 18 1 0 0 0 0 9 23 1 0 0 0 0 10 19 2 0 0 0 0 10 24 1 0 0 0 0 12 26 2 0 0 0 0 13 26 1 0 0 0 0 14 27 2 0 0 0 0 15 27 1 0 0 0 0 16 28 2 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 25 1 0 0 0 0 20 29 1 0 0 0 0 21 31 2 0 0 0 0 21 32 1 0 0 0 0 25 11 1 6 0 0 0 25 33 1 0 0 0 0 26 36 1 0 0 0 0 27 37 1 0 0 0 0 28 38 1 0 0 0 0 29 39 1 1 0 0 0 30 34 1 0 0 0 0 30 40 2 0 0 0 0 31 33 1 0 0 0 0 31 41 1 0 0 0 0 32 34 2 0 0 0 0 32 43 1 0 0 0 0 33 35 2 0 0 0 0 34 35 1 0 0 0 0 35 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.23
Volume:	610.465
LogP:	5.212
LogD:	3.855
LogS:	-3.334
# Rotatable Bonds:	12
TPSA:	147.68
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.084
Synthetic Accessibility Score:	3.786
Fsp3:	0.171
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.53
MDCK Permeability:	9.210900316247717e-06
Pgp-inhibitor:	0.352
Pgp-substrate:	0.733
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	101.8393783569336%
Volume Distribution (VD):	0.268
Pgp-substrate:	0.4904455840587616%

ADMET: Metabolism

CYP1A2-inhibitor:	0.612
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.817
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.928
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.504
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.462

ADMET: Excretion

Clearance (CL):	11.856
Half-life (T1/2):	0.852

ADMET: Toxicity

hERG Blockers:	0.305
Human Hepatotoxicity (H-HT):	0.35
Drug-inuced Liver Injury (DILI):	0.563
AMES Toxicity:	0.775
Rat Oral Acute Toxicity:	0.27
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.967
Carcinogencity:	0.254
Eye Corrosion:	0.003
Eye Irritation:	0.614
Respiratory Toxicity:	0.388

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC43345

Natural Product ID:	NPC43345
*Common Name:**	Calyxin A
IUPAC Name:	(E)-1-[2,4-dihydroxy-3-[(E,3R,5S)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hept-1-en-3-yl]-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	QFJRXXRSLNGSSQ-UCLDVTQQSA-N
Standard InCHI:	InChI=1S/C35H34O8/c1-43-32-21-31(41)33(35(42)34(32)30(40)19-10-24-7-16-28(38)17-8-24)25(11-2-22-3-12-26(36)13-4-22)20-29(39)18-9-23-5-14-27(37)15-6-23/h2-8,10-17,19,21,25,29,36-39,41-42H,9,18,20H2,1H3/b11-2+,19-10+/t25-,29-/m0/s1
SMILES:	COc1cc(O)c(c(c1C(=O)/C=C/c1ccc(cc1)O)O)[C@H](C[C@H](CCc1ccc(cc1)O)O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504530
PubChem CID:	10817087
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	10.7	uM	PMID[458820]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	13.1	uM	PMID[458820]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC43345 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	1444
0.2-0.3	3316
0.3-0.4	8433
0.4-0.5	10430
0.5-0.6	3697
0.6-0.7	5893
0.7-0.8	5969
0.8-0.85	1980
0.85-0.9	892
0.9-0.95	243
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC476553
0.9931	High Similarity	NPC476551
0.9931	High Similarity	NPC476552
0.9732	High Similarity	NPC208258
0.973	High Similarity	NPC79375
0.973	High Similarity	NPC37253
0.9724	High Similarity	NPC152233
0.9667	High Similarity	NPC15815
0.9662	High Similarity	NPC324447
0.9655	High Similarity	NPC475348
0.9655	High Similarity	NPC261271
0.96	High Similarity	NPC257166
0.9536	High Similarity	NPC51247
0.9517	High Similarity	NPC471524
0.9517	High Similarity	NPC471473
0.9517	High Similarity	NPC282957
0.9517	High Similarity	NPC471523
0.9517	High Similarity	NPC194949
0.9474	High Similarity	NPC98023
0.9474	High Similarity	NPC195136
0.9474	High Similarity	NPC226462
0.947	High Similarity	NPC1796
0.9408	High Similarity	NPC105584
0.9408	High Similarity	NPC90497
0.94	High Similarity	NPC121568
0.9396	High Similarity	NPC178484
0.9346	High Similarity	NPC42965
0.9346	High Similarity	NPC121647
0.9342	High Similarity	NPC475184
0.931	High Similarity	NPC26238
0.9276	High Similarity	NPC56049
0.9276	High Similarity	NPC54830
0.9226	High Similarity	NPC473012
0.9216	High Similarity	NPC324358
0.9216	High Similarity	NPC323627
0.9216	High Similarity	NPC322459
0.9216	High Similarity	NPC318527
0.9205	High Similarity	NPC208011
0.9205	High Similarity	NPC115601
0.9205	High Similarity	NPC39154
0.9205	High Similarity	NPC78324
0.9189	High Similarity	NPC25844
0.9184	High Similarity	NPC117836
0.9184	High Similarity	NPC476178
0.9184	High Similarity	NPC475705
0.9184	High Similarity	NPC51887
0.9178	High Similarity	NPC476508
0.9178	High Similarity	NPC321980
0.9178	High Similarity	NPC470087
0.9172	High Similarity	NPC470211
0.9172	High Similarity	NPC251336
0.9167	High Similarity	NPC473009
0.9161	High Similarity	NPC301256
0.9161	High Similarity	NPC312273
0.915	High Similarity	NPC32867
0.915	High Similarity	NPC69531
0.9133	High Similarity	NPC3642
0.9116	High Similarity	NPC297600
0.911	High Similarity	NPC259166
0.911	High Similarity	NPC144118
0.911	High Similarity	NPC213659
0.911	High Similarity	NPC215311
0.911	High Similarity	NPC204985
0.911	High Similarity	NPC219917
0.911	High Similarity	NPC48624
0.911	High Similarity	NPC80962
0.911	High Similarity	NPC172250
0.911	High Similarity	NPC326109
0.9108	High Similarity	NPC473010
0.9103	High Similarity	NPC251681
0.9103	High Similarity	NPC243528
0.9091	High Similarity	NPC287789
0.9091	High Similarity	NPC271741
0.9085	High Similarity	NPC150908
0.9085	High Similarity	NPC215203
0.9085	High Similarity	NPC14606
0.9085	High Similarity	NPC159707
0.9085	High Similarity	NPC158027
0.9085	High Similarity	NPC121649
0.9085	High Similarity	NPC134171
0.9085	High Similarity	NPC248739
0.9085	High Similarity	NPC265624
0.9085	High Similarity	NPC182555
0.9085	High Similarity	NPC205026
0.9085	High Similarity	NPC52611
0.9085	High Similarity	NPC100049
0.9085	High Similarity	NPC66441
0.9085	High Similarity	NPC300668
0.9085	High Similarity	NPC186227
0.9079	High Similarity	NPC174086
0.9067	High Similarity	NPC122894
0.906	High Similarity	NPC228779
0.906	High Similarity	NPC470133
0.906	High Similarity	NPC473078
0.906	High Similarity	NPC470131
0.906	High Similarity	NPC470134
0.906	High Similarity	NPC470132
0.906	High Similarity	NPC109183
0.9054	High Similarity	NPC245482
0.9054	High Similarity	NPC301751
0.9048	High Similarity	NPC52789
0.9048	High Similarity	NPC268204
0.9048	High Similarity	NPC55832
0.9048	High Similarity	NPC469404
0.9048	High Similarity	NPC470089
0.9048	High Similarity	NPC26051
0.9041	High Similarity	NPC295384
0.9041	High Similarity	NPC283429
0.9041	High Similarity	NPC477956
0.9034	High Similarity	NPC153979
0.9034	High Similarity	NPC322301
0.9034	High Similarity	NPC255801
0.9032	High Similarity	NPC324736
0.9032	High Similarity	NPC51760
0.9032	High Similarity	NPC295090
0.9026	High Similarity	NPC309648
0.9026	High Similarity	NPC471787
0.9026	High Similarity	NPC61112
0.9026	High Similarity	NPC198489
0.902	High Similarity	NPC71061
0.902	High Similarity	NPC290830
0.902	High Similarity	NPC194593
0.902	High Similarity	NPC72425
0.902	High Similarity	NPC303485
0.9013	High Similarity	NPC204561
0.9013	High Similarity	NPC317715
0.9013	High Similarity	NPC148945
0.9013	High Similarity	NPC78835
0.9013	High Similarity	NPC316960
0.9013	High Similarity	NPC309512
0.9007	High Similarity	NPC473016
0.9007	High Similarity	NPC132345
0.9007	High Similarity	NPC89442
0.9	High Similarity	NPC51070
0.9	High Similarity	NPC222298
0.8993	High Similarity	NPC271288
0.8993	High Similarity	NPC197252
0.8993	High Similarity	NPC235217
0.8993	High Similarity	NPC473015
0.8993	High Similarity	NPC328623
0.8993	High Similarity	NPC473013
0.8993	High Similarity	NPC470136
0.8993	High Similarity	NPC470135
0.8993	High Similarity	NPC236766
0.8993	High Similarity	NPC39045
0.8993	High Similarity	NPC476055
0.8993	High Similarity	NPC473014
0.8986	High Similarity	NPC148545
0.898	High Similarity	NPC11056
0.898	High Similarity	NPC265178
0.898	High Similarity	NPC101366
0.898	High Similarity	NPC253822
0.8973	High Similarity	NPC21350
0.8966	High Similarity	NPC41461
0.8966	High Similarity	NPC477244
0.8966	High Similarity	NPC213603
0.8966	High Similarity	NPC25287
0.8966	High Similarity	NPC249606
0.8966	High Similarity	NPC274109
0.8966	High Similarity	NPC12165
0.8966	High Similarity	NPC98115
0.8966	High Similarity	NPC168105
0.8966	High Similarity	NPC477243
0.8966	High Similarity	NPC24394
0.8966	High Similarity	NPC66349
0.8966	High Similarity	NPC186838
0.8966	High Similarity	NPC1486
0.8966	High Similarity	NPC150399
0.8966	High Similarity	NPC477242
0.8961	High Similarity	NPC66508
0.8961	High Similarity	NPC226656
0.8961	High Similarity	NPC201227
0.8961	High Similarity	NPC258474
0.8947	High Similarity	NPC177308
0.8947	High Similarity	NPC124478
0.8944	High Similarity	NPC477529
0.894	High Similarity	NPC145467
0.894	High Similarity	NPC39195
0.894	High Similarity	NPC160821
0.894	High Similarity	NPC6511
0.894	High Similarity	NPC132592
0.8933	High Similarity	NPC477955
0.8933	High Similarity	NPC476088
0.8933	High Similarity	NPC472629
0.8933	High Similarity	NPC474161
0.8933	High Similarity	NPC127059
0.8933	High Similarity	NPC316769
0.8933	High Similarity	NPC285630
0.8926	High Similarity	NPC185276
0.8926	High Similarity	NPC107177
0.8926	High Similarity	NPC143896
0.8926	High Similarity	NPC85162
0.8926	High Similarity	NPC125894
0.8926	High Similarity	NPC75049
0.8926	High Similarity	NPC149026
0.8926	High Similarity	NPC150408
0.8926	High Similarity	NPC91560
0.8926	High Similarity	NPC39329
0.8926	High Similarity	NPC257097
0.8926	High Similarity	NPC81697

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC43345 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	935
0.2-0.3	1435
0.3-0.4	2585
0.4-0.5	2042
0.5-0.6	1204
0.6-0.7	409
0.7-0.8	162
0.8-0.85	26
0.85-0.9	14
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9338	High Similarity	NPD8443	Clinical (unspecified phase)
0.8947	High Similarity	NPD4380	Phase 2
0.8903	High Similarity	NPD7768	Phase 2
0.8868	High Similarity	NPD7852	Clinical (unspecified phase)
0.8867	High Similarity	NPD7410	Clinical (unspecified phase)
0.8767	High Similarity	NPD1510	Phase 2
0.8766	High Similarity	NPD7411	Suspended
0.8679	High Similarity	NPD6959	Discontinued
0.8654	High Similarity	NPD7819	Suspended
0.8621	High Similarity	NPD1240	Approved
0.8618	High Similarity	NPD4378	Clinical (unspecified phase)
0.8608	High Similarity	NPD7075	Discontinued
0.8591	High Similarity	NPD1549	Phase 2
0.8523	High Similarity	NPD1552	Clinical (unspecified phase)
0.8523	High Similarity	NPD1550	Clinical (unspecified phase)
0.8503	High Similarity	NPD1607	Approved
0.8456	Intermediate Similarity	NPD2796	Approved
0.8418	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7473	Discontinued
0.8354	Intermediate Similarity	NPD6801	Discontinued
0.8293	Intermediate Similarity	NPD6166	Phase 2
0.8293	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD6651	Approved
0.8194	Intermediate Similarity	NPD7390	Discontinued
0.8171	Intermediate Similarity	NPD6232	Discontinued
0.817	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD3749	Approved
0.8125	Intermediate Similarity	NPD1934	Approved
0.8049	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD3750	Approved
0.7988	Intermediate Similarity	NPD7074	Phase 3
0.7987	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2935	Discontinued
0.7962	Intermediate Similarity	NPD6799	Approved
0.7941	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7458	Discontinued
0.7929	Intermediate Similarity	NPD5844	Phase 1
0.7929	Intermediate Similarity	NPD7054	Approved
0.7925	Intermediate Similarity	NPD5403	Approved
0.7908	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD8313	Approved
0.7907	Intermediate Similarity	NPD8312	Approved
0.7898	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6559	Discontinued
0.7888	Intermediate Similarity	NPD6599	Discontinued
0.7885	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7472	Approved
0.787	Intermediate Similarity	NPD3818	Discontinued
0.7866	Intermediate Similarity	NPD3882	Suspended
0.7853	Intermediate Similarity	NPD2801	Approved
0.7852	Intermediate Similarity	NPD4908	Phase 1
0.7849	Intermediate Similarity	NPD7808	Phase 3
0.7849	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1511	Approved
0.7821	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2800	Approved
0.7799	Intermediate Similarity	NPD2533	Approved
0.7799	Intermediate Similarity	NPD5401	Approved
0.7799	Intermediate Similarity	NPD2534	Approved
0.7799	Intermediate Similarity	NPD2532	Approved
0.7792	Intermediate Similarity	NPD2799	Discontinued
0.7791	Intermediate Similarity	NPD7251	Discontinued
0.7784	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7003	Approved
0.775	Intermediate Similarity	NPD1512	Approved
0.7748	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5404	Approved
0.7742	Intermediate Similarity	NPD1551	Phase 2
0.7742	Intermediate Similarity	NPD5408	Approved
0.7742	Intermediate Similarity	NPD5405	Approved
0.7742	Intermediate Similarity	NPD5406	Approved
0.7733	Intermediate Similarity	NPD5953	Discontinued
0.7733	Intermediate Similarity	NPD6797	Phase 2
0.7718	Intermediate Similarity	NPD2798	Approved
0.7697	Intermediate Similarity	NPD5402	Approved
0.7697	Intermediate Similarity	NPD3817	Phase 2
0.7692	Intermediate Similarity	NPD2344	Approved
0.7677	Intermediate Similarity	NPD3748	Approved
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7636	Intermediate Similarity	NPD8455	Phase 2
0.7616	Intermediate Similarity	NPD7286	Phase 2
0.7611	Intermediate Similarity	NPD4360	Phase 2
0.7611	Intermediate Similarity	NPD4363	Phase 3
0.7607	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD3226	Approved
0.7595	Intermediate Similarity	NPD1243	Approved
0.7593	Intermediate Similarity	NPD920	Approved
0.7593	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD8151	Discontinued
0.7543	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD943	Approved
0.7527	Intermediate Similarity	NPD7871	Phase 2
0.7527	Intermediate Similarity	NPD7870	Phase 2
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7473	Intermediate Similarity	NPD7697	Approved
0.7473	Intermediate Similarity	NPD7698	Approved
0.7473	Intermediate Similarity	NPD7696	Phase 3
0.7472	Intermediate Similarity	NPD8150	Discontinued
0.7469	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6778	Approved
0.7405	Intermediate Similarity	NPD6780	Approved
0.7405	Intermediate Similarity	NPD6776	Approved
0.7405	Intermediate Similarity	NPD6782	Approved
0.7405	Intermediate Similarity	NPD6779	Approved
0.7405	Intermediate Similarity	NPD6781	Approved
0.7405	Intermediate Similarity	NPD6777	Approved
0.7403	Intermediate Similarity	NPD2313	Discontinued
0.7384	Intermediate Similarity	NPD3926	Phase 2
0.7383	Intermediate Similarity	NPD1610	Phase 2
0.7383	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7435	Discontinued
0.7377	Intermediate Similarity	NPD4361	Phase 2
0.7377	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5124	Phase 1
0.7372	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD37	Approved
0.7342	Intermediate Similarity	NPD7033	Discontinued
0.7333	Intermediate Similarity	NPD3972	Approved
0.7326	Intermediate Similarity	NPD7229	Phase 3
0.7318	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6273	Approved
0.7316	Intermediate Similarity	NPD7701	Phase 2
0.7305	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1203	Approved
0.7303	Intermediate Similarity	NPD1470	Approved
0.7292	Intermediate Similarity	NPD7801	Approved
0.729	Intermediate Similarity	NPD3764	Approved
0.729	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7267	Intermediate Similarity	NPD7199	Phase 2
0.7267	Intermediate Similarity	NPD1201	Approved
0.7267	Intermediate Similarity	NPD2654	Approved
0.7263	Intermediate Similarity	NPD7584	Approved
0.7257	Intermediate Similarity	NPD7177	Discontinued
0.7257	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD919	Approved
0.725	Intermediate Similarity	NPD2346	Discontinued
0.724	Intermediate Similarity	NPD7874	Approved
0.724	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4965	Approved
0.7235	Intermediate Similarity	NPD4967	Phase 2
0.7235	Intermediate Similarity	NPD4966	Approved
0.7234	Intermediate Similarity	NPD6823	Phase 2
0.7225	Intermediate Similarity	NPD5710	Approved
0.7225	Intermediate Similarity	NPD5711	Approved
0.7219	Intermediate Similarity	NPD1465	Phase 2
0.7219	Intermediate Similarity	NPD5761	Phase 2
0.7219	Intermediate Similarity	NPD5760	Phase 2
0.7219	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7699	Phase 2
0.7204	Intermediate Similarity	NPD7700	Phase 2
0.7198	Intermediate Similarity	NPD4287	Approved
0.719	Intermediate Similarity	NPD1164	Approved
0.719	Intermediate Similarity	NPD2797	Approved
0.7168	Intermediate Similarity	NPD1247	Approved
0.716	Intermediate Similarity	NPD7577	Discontinued
0.7159	Intermediate Similarity	NPD7228	Approved
0.7159	Intermediate Similarity	NPD3751	Discontinued
0.7158	Intermediate Similarity	NPD8320	Phase 1
0.7158	Intermediate Similarity	NPD8319	Approved
0.7151	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6535	Approved
0.7135	Intermediate Similarity	NPD6534	Approved
0.7126	Intermediate Similarity	NPD3787	Discontinued
0.7124	Intermediate Similarity	NPD1876	Approved
0.7115	Intermediate Similarity	NPD3027	Phase 3
0.7114	Intermediate Similarity	NPD1548	Phase 1
0.7114	Intermediate Similarity	NPD9545	Approved
0.7113	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7783	Phase 2
0.7105	Intermediate Similarity	NPD9717	Approved
0.7095	Intermediate Similarity	NPD7685	Pre-registration
0.7095	Intermediate Similarity	NPD9493	Approved
0.7091	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD1729	Discontinued
0.7076	Intermediate Similarity	NPD4288	Approved
0.707	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6798	Discontinued
0.7069	Intermediate Similarity	NPD8127	Discontinued
0.7059	Intermediate Similarity	NPD6844	Discontinued
0.7044	Intermediate Similarity	NPD6355	Discontinued
0.7044	Intermediate Similarity	NPD230	Phase 1
0.7032	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD651	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data